Sulfuric Acid → 1H-Imidazole-4-sulfonic acid, 5-chloro-1-methyl-

Reaction equation

[Cl:1][C:2]1[N:6]([CH3:7])[CH:5]=[N:4][CH:3]=1.[S:8](=O)(=[O:11])([OH:10])[OH:9]>>[Cl:1][C:2]1[N:6]([CH3:7])[CH:5]=[N:4][C:3]=1[S:8]([OH:11])(=[O:10])=[O:9]

Participants

Reactant 2

HCID 1118Sulfuric Acid

HCID 701055-chloro-1-methyl-1H-imidazole

Product 1

HCID 30781001H-Imidazole-4-sulfonic acid, 5-chloro-1-methyl-

Procedure

33 g (0.28 mol) of 5-chloro-1-methylimidazole in 200 ml of fuming sulfuric acid are heated at 160°-180° C. for 4 hours. After cooling, the reaction mixture is cautiously added to ice. The product crystallizes out from the cold aqueous solution (about 1.5 l). After recrystallizing twice from water, the title compound is obtained in the form of coarse yellowish crystals of melting point 309°-310° C.

Workup

temperatureAfter cooling
additionthe reaction mixture is cautiously added to ice
customThe product crystallizes out from the cold aqueous solution (about 1.5 l)
customAfter recrystallizing twice from water

Sources & evidence

ORD record: ord-faf639ffcc1645899c5ac0bf829f29fa
Source dataset: uspto-grants-1993_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05232922

Reaction notes

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